Skip to main content
Chemistry LibreTexts

Reactions of Alkenes with Halogens

  • Page ID
    3882
  • \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}} } \) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash {#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\)

    In each case, we will look at ethene as typical of all of the alkenes. There are no complications as far as the basic facts are concerned as the alkenes get bigger.

    Ethene and fluorine

    Ethene reacts explosively with fluorine to give carbon and hydrogen fluoride gas. This isn't a useful reaction.

    \[\ce{CH2=CH2 + 2F2 -> 2C + 4HF}\]

    Ethene and Chlorine or Bromine or Iodine

    In each case you get an addition reaction. For example, bromine adds to give 1,2-dibromoethane.

    padding.gifethenebr2.gif

    The reaction with bromine happens at room temperature. If you have a gaseous alkene like ethene, you can bubble it through either pure liquid bromine or a solution of bromine in an organic solvent like tetrachloromethane. The reddish-brown bromine is decolourized as it reacts with the alkene. A liquid alkene (like cyclohexene) can be shaken with liquid bromine or its solution in tetrachloromethane. Chlorine reacts faster than bromine, but the chemistry is similar. Iodine reacts much, much more slowly, but again the chemistry is similar. You are much more likely to meet the bromine case than either of these.

    Alkenes decolorize bromine water.

    If you shake an alkene with bromine water (or bubble a gaseous alkene through bromine water), the solution becomes colorless. This is complicated by the fact that the major product is not 1,2-dibromoethane. The water also gets involved in the reaction, and most of the product is 2-bromoethanol.

    padding_q6hd.gifethenebrwater.gif

    However, there will still be some 1,2-dibromoethane formed, so at this sort of level you can probably get away with quoting the simpler equation:

    padding_tuxn.gifethenebr2_blqb.gif

    Contributors


    This page titled Reactions of Alkenes with Halogens is shared under a CC BY-NC 4.0 license and was authored, remixed, and/or curated by Jim Clark.

    • Was this article helpful?